27 CHRISTOPHER STREET

In September 2014, the foster and child-care agency New York Foundling, one of the city’s oldest charities, sold its Greenwich Village building for a staggering $45 million to an unknown buyer with the intention of converting it into a single-family mansion. It will be among the most expensive single-family residences ever purchased in Manhattan.

The four-story, limestone and brick property on the northeast corner of Christopher Street and Waverly Place sits within the beloved Greenwich Village Historic District, and currently the owner is seeking approvals from the Landmarks Preservation Commission to add a pergola, mechanical equipment and an elevator bulkhead to the roof. Yet-to-be-approved permits were filed in November by HS Jessup Architecture, detailing a sprawling home of five floors and 15,000 square feet of floor area. Plans on Jessup’s website show the mansion will have six bedrooms, two kitchens, its own elevator, a dressing room and walk-in closet larger than most apartments, a 50-foot lap pool, and more than 4,000 square-feet of outdoor space that will include a rooftop terrace. The architect also handled the neo-traditional penthouse addition atop 345 West 13th Street in the Meatpacking District.

For Manhattan’s jet-set crowd, the 2010s are starting to look an awful lot like the 1900s.

New York’s upper crust are embracing a return to the Gilded Age, moving out of their fancy penthouses, co-ops and lofts and into opulent single-family mansions. From Aby Rosen’s quest to build the largest private mansion on Park Avenue to Jared Kushner’s conversion of three former Brooklyn Law School buildings into single-family townhouses—the most affluent buyers are now on the hunt for New York’s ultimate trophy prize.